


My boys

by Iliketowrite_2



Category: Supernatural
Genre: Angst, Comfort, Crying, Eating out, Fingering, First Orgasm, First Time writing Smut, Fluff, Fluffy, Multi, NSFW, No Wincest, Poly fic, Polyamorous relationship, Reader Insert, Smut, Smutty, Use of Safe Word, Vibrator, Virgin Reader, angsty, virgin, virgin!reader
Language: English
Status: Completed
Published: 2018-09-10
Updated: 2018-09-10
Packaged: 2019-07-10 17:44:59
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,440
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15954365
Author URL: https://archiveofourown.org/users/Iliketowrite_2/pseuds/Iliketowrite_2
Summary: You’ve dated the Winchester brothers for a while, but you’d never gotten to do anything dirty in the bedroom for a reason.You’re a virgin.





	My boys

**Author's Note:**

> This is my first time ever writing or attempting smut, so I hope it’s okay. 
> 
> Sorry for any spelling mistakes :)  
> This fic has 4,441 words... sheesh. 
> 
> Off ya go. Go read!

You run your towel through your dripping hair as you sigh, you’d been trying this new technique for weeks now, and you still couldn’t get the satisfaction you craved. Damnit! You deserved to orgasm! Just once!  
Your face was hot and sweaty as you got dressed and opened the bathroom door, the cool fresh air in the bunker calming your heated skin almost instantly. As you started walking down the hallway you stopped as you heard your name being called out. 

“Hey Y/n,” you turned around to see Dean and Sam, side by side, smirking at you. You furrowed your brows, looking at them in confusion. Why are they looking at me like that?  
“What?” You bit out, frustrated and horny; still confused as to why they were looking like smug looking gods.   
You’d been dating the Winchester’s for a few months now, having grown up together as kids you all had a really strong bond, and you only reconnected a couple years ago after you’d been separated; moved from place to place- or should I say- motel to motel is more like it.   
“See, we couldn’t help but overhear your little... problem.” Dean replied, his lips twisting into a cruel, teasing smile.   
“Jesus Christ, you were listening to me?! What the fuck is wrong with you, have you never heard of privacy?” You snapped, stomping your foot as you whipped around and trudged towards your room, slamming the door as if to say ‘y’all better fuck off’. 

You quickly got dressed into your night shorts and a tank top, not bothering to put on a bra or underwear. They were damn uncomfortable. Lying down on your bed you whined in frustration into your pillow, kicking your legs like a five year old having a tantrum. Seriously, you’d spent years masturbating, and yet you’ve never orgasmed. What’s with that? Of course, you can bring yourself to the verge of orgasming, but you always got overwhelmed with the amazing and intense sensation, that you stopped, right before you reached your peak. 

You want to orgasm, but you just... can’t. Can’t bring yourself to push through that intense and torturous feeling. 

There was a soft knock on your door thirty or so minutes later, and you sighed.   
“Go away, Dean” You didn’t feel like dealing with his teasing tonight. You were tense and on edge after a hunt that almost went wrong in every single possible way.   
The door cracked open as Sam peeked his head through,  
“It’s just me,” He walked in the rest of the way and shut the door behind him, sitting on the edge and rubbing your thigh. “What’s up Y/n/n? What’s going on? You haven’t come to our room yet. I don’t even remember the last time we haven’t all slept in the same room.” He was concerned but also slightly amused, but he pushed that side down, for your sake.   
Sam, Dean, and yourself had shared a room for about a month now, not to do anything in that sense, but since you’d gotten together you all liked being together. You were a cuddler. You liked being close to them, knowing that they’re with you.   
But despite Deans sexual nature and endless flirting, none of you had ever slept together. You were hesitant to let them into that part of your life just in case they make fun of your... inexperience. Of course, Sam and Dean would never sleep together, but they both expressed how they both wanted you. You didn’t want to let them down; and before you slept with them, you wanted to know what an orgasm felt like. You wanted some experience, it was embarrassing enough being a virgin, but not even knowing what it felt like to cum?

“I’m.. just... I’m embarrassed Sam.”  
“Why? Because we heard you? Sweetheart you shouldn’t be embarrassed. We understand that you have needs and wants, and if you enjoy it, why not? There’s nothing wrong with touching yourself.”  
“I know, I know that. But that’s not what I’m worried about.”  
“What is it then?” The genuine concern and love pouring out of this man never failed to make your heart flutter and your stomach twist with butterflies.   
“I...I want to be with you and Dean.”  
“You are with us Y/n, we’ve been together for-“  
“I know that Sam, I want to have sex with you and Dean! I want to be with you! But I can never bring myself to do it because I’ve never slept with anybody, I’ve never been touched by anybody, I’ve never even cum before! I just wanna be able to make you happy.” You stand as you rant, throwing your hands around wildly, wrapping them around yourself once you’d finished talking. You felt so exposed right now as you sat down on the table beside your bed. You ran your hands over your face as you breathed out, “I just don’t wanna do or say something stupid because I have no experience. And I know Dean would never let me hear the end of it if he knew. I want to be good enough for you but I have nothing to offer.” You didn’t expect to burst into tears over something so stupid, but it wasn’t stupid. Not to you anyway. 

Sam immediately got up and came around the bed, enveloping you into his arms and pulling you into his lap as he sat back down onto the bed. He rubs his hand up and down your back, gently shushing you as you grasp onto his soft flannel shirt.   
“Oh oh oh Y/n/n, sweetheart no. No, no, no don’t you think like that. There’s nothing wrong with any of the things you just told me. Just you dating Dean and I makes us the happiest people in the world. We don’t need sex to make us love you more. That’s not possible baby.   
It’s okay. You don’t have to be experienced, and it’ll actually help us feel special being your firsts. I promise you, no matter what you might think, we love you, and the way you can get more experience, is to experience it. But you only do what you’re ready for, and if you feel like you need to make yourself cum before you have sexual relations with either of us, then we can wait for you. But if you’re only doing that so you can impress us or because you’re scared we’ll judge you, then you don’t know us. We’d take care of you sweetheart.”

You hadn’t even noticed Dean until he spoke up,   
“Sweetie... do you really think I’d make fun of you?” He looked heartbroken and you wondered how much he’d heard.   
“I just-“ I sniffled as I wiped my nose, “I know you like girls with experience, and I know Sam likes.. flexible girls. I’m not either of those. I want to be special for you.”  
“But you are special to us. Just being with you is so special. You’re important to us, and I never want you to feel like I’d judge you for something like this.”  
You nod as he wipes the tears from your face and he smiles at you and you give him a shaky smile back. Sam squeezes you and lets you go, standing with you. 

“How about we go to bed, huh?” Sam grabs your hand and you pull back.   
“No I want.. I want you to help me.” You whispered the last part of the sentence, half hoping they wouldn’t hear and half hoping they would so you wouldn’t have to ask again. You lifted your eyes to theirs and they look partially shocked. “Please?” You ask desperately.   
“Are you sure? Are you ready for this?” Dean places his hands on your forearms, gently leaning down a bit to look you in the eyes better. You nod hesitantly. Dean smiles sadly and shakes his head.   
“No you’re not. And that’s okay.” You can’t help but feel conflicted. You were disappointed, but you knew you weren’t exactly ready for having sex yet.   
“Okay.. I might go to bed then.. I’ll probably be asleep when you guys come to bed, so I’ll.. goodnight.”  
You head towards your shared bedroom but Sam held you still.   
“Y/n, how do you feel about trying something else?”  
“Something else?”

Sam looked towards Dean and they had a silent conversation with their eyes. Stupid Winchester’s and their stupid ability to talk without talking. Sam raises his eyebrows and Dean nods in agreement.   
“Do you trust us?” Sam continues. You pause for a second as you looked at them with curiosity.  
“Yes?...”  
“Y/n/n, we need to know that you’re okay with us doing things to you.” Dean added sternly. “We need a yes or no. It’s okay if it’s a no, but we don’t want you to feel forced to do anything you’re not ready or wanting to do.”

You think about your relationship with the boys. You’ve always wanted to get closer to them in a sexual way. You’ve been with them for a while. You know they love and respect you and your opinions. And you know they’d give themselves up for you in a heartbeat. 

“Yes. I trust you.”   
“Come with us.” Sam and Dean grab a hand each and lead you past your shared bedroom and down the halls, further than you’d ever gone before.   
“Where are we-“  
“You’ll see,” dean squeezed your hand as they continued leading you down the halls.   
They lead you for what felt like forever before they stopped outside of a door. You looked at both of them as they nodded at each other. Dean reached for the handle with his spare hand and pushed the door open. Your mouth dropped as you saw what was inside. 

“We have a sex dungeon? We-“ you pointed to Sam, Dean, and then yourself, pointing between the three of you. “-have a sex dungeon. How long has this been here?!” They chuckled.   
“Long enough” they led you into the room and you look around. The walls were covered in leather whips, blindfolds, restraints, ropes, plugs, dildos, vibrators- you name it, they probably have it. ‘Holy crap’ you whisper under your breath. 

“Safe word.” Dean said, you turn back to look at him.   
“Safe word?” Sam laughs gently,  
“He means, if you want to stop, at any time, you say this word and we’ll stop for whatever reason, whenever it happens. Preferably choose something you wouldn’t usually say during sex.. or stuff like that.”  
“What, like pasta?” They both laugh at that,  
“If that’s what you want to use.” Sam chuckled.   
“No.. no I wanna use something else.. uhh... can’t I just say stop?”  
“No.” They both say in unison. Dean continues to explain,  
“Sometimes people say stop when something feels good, so it’s better to have a word that’s out of the ordinary.”  
“How about.. red? Like, just plain ol’ red?”   
“Sure. Sounds pretty obvious, and we won’t need colours with what we’re doing today.” Sam smiled,  
“Wait what uses colour?”   
“You have so much to learn Y/n/n..”

You look down at that. Dean grabs your chin and pulls your face up to meet his.   
“It’s okay.”   
“Alright, you ready sweetheart?” Sam coo’s. You nod at him nervously. Dean takes hold of your shoulders and rubs them,   
“Relax Y/n. We’ll take good care of you.” Sam shuts the door and walks over to the bed in the middle of the giant room. He pats the space next to him, and you walk over, sitting down next to him. He kisses your forehead as dean goes to the wall of objects and picks a few things down. You looked over towards the noises in curiosity before Sam pulled your face to his and his lips met yours in a hot but gentle kiss. 

You had make out sessions with them before, sure. You had never let it get past pashing. You’d seen both of them naked, both proud with how they looked and confident with their bodies. They’d seen you in shorts and a tank. At best. Maybe in a bra or underwear if you needed to be patched up from a rough hunt. 

Sam pushed you onto your back onto the bed and pushed his hands up under your shirt, gently cupping your breast and kneading it in his hand. He pulls away from the kiss and lifts your arms up, pulling the tank with it. As soon as the top is off you reach to cover up but Sam holds your hands back.   
“No. Don’t.” He said, his eyes falling on your breasts, floating down your stomach and to the only thing you have left on your body. “You’re so beautiful,”  
“You got that right.” Dean groans. 

Sam stands from the bed and sorts through the pile Dean left on the metal restraining chair next to the bed as Dean replaces Sam and slowly starts to suck on your neck, down to the side of your chest, down the stomach to the ribbon of your night shorts. He looks up at you with gleaming eyes as he bites down on the fabric of the shorts and slowly starts pulling them down. You lift your backside up as he pulls them down your legs and drops them out of his mouth. He crawls back up the bed like a predator and nips your ear,  
“You are so fucking perfect.” You growl as he lightly feathers his fingers over your inner thigh.   
“You ready baby girl?” You nod at him, eyes closed in lust and slight fear but excitement of what might happen next. He gets off you and your eyes snap open, they’re both standing at the end of the bed just looking at you, you sit up and cover your chest and cross your legs.   
“What?” You stammer anxiously, did they not like it? You?  
Dean walks to the head of the bed and sits down behind you pulling you with him to lean against the headboard, your bare back on his chest.   
“Wait Wait Wait, Aren’t you guys gonna, you know, strip too?”  
“No sweetheart, this is all about you,”  
“But what if I want it? Please? At least take your shirts off..”  
They groan as the both take off their shirts and toss them to the side.   
“Thank you.” You whisper, taking in the sight of the beauty known as “the Winchester’s”. 

Dean starts to lightly trace his fingers over your ribs, making you wriggle a bit before you adjust to the funny sensation. Sam starts running his hands up and down your thigh, making sure to avoid your perfectly bare mound. Your breathing starts to quicken slightly, getting deeper and heavier. This felt good.   
Dean places his lips on your neck and sucks gently, licking as he pulled away, only to find a new patch of skin to mark. You rest your head on his shoulder, panting as he countinues sucking and dancin his fingers up and down your ribs.   
You gasp and jump up as you feel sam drag his thumb painfully slow up your folds and landing on your clit.   
“Already so wet for us kitten,”  
He pressed his thumb down into your clit and your body jumps up in surprise, Dean reaches over to the side table and pulls something over. He puts it in front of you so you can see.   
“What-“  
“One cuff goes around the ankle, the other around the wrist. There’s one for both sides.” He explains as he sits up against the head rest, pulling you with him until the only part of your body on an angle was below the waist, your cunt still facing directly towards Sam. Dean leans down and cuffs your left ankle to your left wrist, and does the same to the other leg and wrist.   
“What’s your Safe word sweetheart.” Sam wasn’t asking, he was just making sure that I remembered it.   
“Red.”  
“Good. Get ready sweetheart.”  
“Get ready for w-UH!” You moan as he presses his tongue hard into your clit, swirling it around like a loose bead on some string. Your legs open wider to inside him in, and you throw your head back again. Dean wraps his arms under yours and grabs your breasts, twirling your hardened nipples around in his thumb and index fingers.   
“Uuuuuuuuuuuuuhhh” You moaned as Dean continued teasing your nipples between his fingers. Sam thrusts his pointer finger into your dripping wet slit, as he continued to nip and suck at your sensitive and swollen clit. Sam curls his finger up and rubs the top of your walls, making your hips jerk upward into his face.   
“Stay.” He growled.   
“Dean!” you gasped as he moved from behind you an let you fall into the pillows behind you.   
“Ahhhh saaam,” You whined pushing your dripping pussy down, in hopes to get him to move faster. He pushed you back and holds you there, glaring up at you.   
“I said stay.” Nipped at your clit and you yelped, he smirked up at you as he slipped two fingers back into you. 

God it was hot in here. Was it hot in here? You were sweating and you vagina felt like it was pulsing with pleasure and want. Need.   
Dean crawled on the bed next to you, before his mouth fell onto your nipples and he started sucking and flicking the buds with his tongue.   
“Mmmmmh!” You forced your eyes shut. There was so much going on, it was overwhelming, but it felt so good..

Sam pulled away and you whimpered at the loss of his touch. You focus of Dean and how he’s gently nipping and starting to pull as he sucked at your nipples. He groaned as he pulled them up and let them go, watching them bounce back and forth before he licks a stripe under your jaw.   
“Ooooooh fuck,” you cursed under your breath. You heard a click before a quiet vibrating noise pulled you out of your daze, and before you could look at what was causing the noise you cried out as a small vibrator was placed over your clit and moved until it was in the most sensitive place. 

Immediately your legs slam shut as you yelp, gasping, you felt out of breath and it was only on you for less than two seconds.   
“Dean.” Sam said sternly, Dean looked up from what he was doing and replied,   
“Got it.” He sat up and leaned over, firmly grabbing your knees and pushing them apart. He stays in that position, forcing your legs open as Sam places the little clip on vibrator back on your clit and turns it on, full speed.   
“AHHHHH!” You mown aloud, thrusting your hips up and trying to escape the incredible torture this machine was putting you through. You push your legs together as hard as you can, but Dean doesn’t let go, he’ll he barely even has to move a muscle to make sure you don’t move.   
“Haaaaaaaaaaa Ohhhh ahhhhhhh Dean!” You yell, shutting your eyes as tightly as you can as your legs shook violently.   
“It’s okay Y/n,” he’s supposed to sound comforting but all you can feel is the intense sensation to get away.   
“Mmmm no, stop.” You ground out, so close to screaming in pain and pleasure it was unreal.   
“It’s okay Y/n, you’re so close, you’re okay.” Sam coo’d loud enough that you could hear over your yelling.   
“Ahhhhhhh haaaaaaaaaah mmmno! Stop, ooooooooh Sam Stop!!” You exclaim pushing and pulling your restraints and shoving your legs against deans legs a shard as you can, bucking to make Sam lose his grip and drop the vibrator.   
“Y/n/n it’s okay, it’s okay baby, it’s okay, you’re just-“  
“RED! RED!!! GET OFF ME, GET IT OFF!!” You screamed to anyone who was listening. 

Immediately the vibrator was off and your legs were free and you clamped them shut. They both worked on either side of you, removing the restraints and you pulled your knees to your chest as you allowed yourself to bawl into your legs.   
“I told you to stop!” You wailed.   
Someone sat next to you and wrapped their arms tightly around you.   
“I’m so sorry Y/n/n. I’m so so sorry. It’s okay baby, it’s okay. It’s all over.” Sam coaxed, rocking you from side to side as you cried into him. Dean must’ve sat on your other side because you felt the bed dip.   
“What happened baby?” He sounded so hurt, knowing that he’d hurt you.   
“It was too much! You might’ve Don’t this before but I haven’t!” You cried out “It was too much! I couldn’t- I couldn’t move! I’ve never done this before Dean! You guys scared me!” 

Their hearts broke at your words and their eyes filled with tears. They scared you. The last thing they’d ever want to do, and they did it. 

“We’re so sorry. We’re so sorry Y/n/n.” Dean whispered.   
“I really wanted to do it, I really wanted to, but i- it felt- I couldn’t - it was too intense, and it scared me. I didn’t know when it’d end of if it’d be too much. I just don’t know that it’s like. I want to know, I want you to show me, but.. I need you to be gentle with me. I’ve never done this before.” You were quiet and ashamed of having to use your Safe word. But that’s what it was there for. And they didn’t look offended, just sad because they knew they could’ve taken it slow. 

“We are so sorry. We understand sweetheart. Next time we’ll make sure to take care of you better Okay? Nothing too intense, just sammy and I. Maybe the vibrator if we need it.”  
“Wait, next time?” You wiped your tears and looked at them. “I thought you were gonna finish..”  
“Sweetie.. you used your Safe word. You got scared. We don’t want that to happen again. At least not today.” Sam said sadly, his eyes big and watery.   
“But I want it.”  
“Y/n.. it’s not a good idea to-“  
“Please?” You looked between them, Puppy dog eyes on full power. 

You watched them as they sighed,  
“Okay. But one more safe word and we’re stopping. Alright?” Dean said sternly. You nodded immediately. You needed this. And you sure as hell wanted it.   
“How about we use vibrator only. Nothing else. Just me, Dean and the vibrator. Dean and I will just be there for support. You’re already sensitive so you shouldn’t need any foreplay anymore. Just all of our attention. Okay?”  
“Okay. I trust you.” You smiled at them and they smiled back.   
“Alright. You tell us when you’re ready and we’ll try again.” You took a deep breath before you breathed out.   
“Okay. I’m ready.”   
“It won’t take long Okay? Just listen to Dean and I. You can do this.” Sam encouraged, nothing but love and care for you in his eyes. You looked over to Dean, finding the same look. You loved these men more than anyone in the world. If they’re with you, you’ll be okay. No matter what. 

“Let’s do this shit.” You states seriously and the boys giggled. Dean took his positions behind you, but instead of holding your breasts, he reaches for your hands. You grip onto them tightly and he holds you tightly to his chest.   
“Deep breaths Y/n. Relax. We got you.” Sam smiled his beautiful smile that put you at ease. You shut your eyes as you lean your head back against Dean.   
“Okay..” you whispered. A silent ‘I’m ready’. 

Sam rubs your legs as he flicks the vibrator back on, he looks up to your face, your eyes closed, head resting on Dean and he knew you were ready. He placed the vibrator back onto your clit and the sensations came flooding back, like it had never stopped. Sam held the vibrator as you pushed your hips back, body trying to get away.   
“Shh you’re okay sweetheart. I got you.” Dean whispered in your ear as he squeezed your hands once. You squeezed back twice as hard, but you didn’t stop.   
“Hmmmm! Ahhhhhhh saaam?” You were writing and squirming, your body going into overdrive as your stomach started to tighten.   
“You’re safe Y/n. I’m right here.” He holds his free hand on your aggressively shaking thigh. You instinctively tried to shut your legs again but Sam gently pried them apart.   
“Just breathe Y/n/n. Deep breaths, you’re okay.”  
“Haaaaaa haaaaaaaaaaa oooooooooooh aaah,” your moaning was getting louder and more desperate by the second, “aaaaah fuck! Sam!” Just then, he pressed a button on the vibrator and the buzzing became so incredible quick, you didn’t even know what hit you.   
“Ooooooh! Ahhhhh! Aaahhhhh! Haaaaaaah! Oh my god, ahhh!”  
“Let go Y/n.” Sam yelled over your screams.   
“OOOOOAAAAAHHHHHHHHHHHH GUYSSS!!!”  
“Cum!” Dean demanded and your body shook and convulsed as a piercing scream filled the air. You felt you body on fire and your clitoris pulsing and contracting incredibly. The feeling of release and the best satisfaction you’d felt in the entirety of your being coursed through your body as you quivered and shook through the afterwaves of what could’ve been the most incredible and intense orgasm anyone had ever had. 

Sam took the vibrator off and put it to the side, smirking at Dean as you panted like a dog who’d just run across the country. Your face was covered in sweat and your eyes were shut tightly, legs still shaking from pleasure and shock. And to them? You’d never looked more beautiful. 

“Ho. Ly. Fuck.” You panted out as you laughed.   
“How was it beautiful?” Dean laughed in amusement.   
“Haaaaaah,” you sighed “that was... fucking incredible!l you laughed out, full of joy. You hadn’t felt this amazing in- well, ever! But dang were you tired. You smiled as you snuggled into Dean, Sam sitting next to you two.   
“I’m a little bit-“ you yawned loudly “sleepy now..” the men chuckled at you.   
“Let’s get you to bed huh?” You nodded at Sam’s question and reached your arms out as he picked you up and held you close in his arms. 

“I love you guys,” you mumble as you struggled to stay awake.   
“We love you too gorgeous.” They said in unison.   
Yep. These were you boys. Forever. 

You spent that night wrapped in their arms, sleeping soundly between the boys you loved most, and who loved you the most.

**Author's Note:**

> Please leave a comment if you liked it! I’d love to know what you thought :)


End file.
